Jon Cryer turns 50 on April 16, and we're celebrating his career with his non-Ducky, non-Alan Harper roles
Credit: Ron Galella, Ltd./WireImage; Rob Latour/Rex USA

Duckie is 50.

Jon Cryer, who turns 50 on April 16, has spent the majority of his life in front of the camera. As his career stands so far, it’s bookended by his two most famous roles: as Duckie Dale in 1986’s Pretty in Pink and as Alan Harper on Two and a Half Men, which just concluded its 12-season run in February.

Of course, he has performed a great many other roles in the 36 years he’s been acting, and in honor of his birthday, we’re saluting the lesser-known but nonetheless great characters of Jon Cryer.

In 1984, Cryer made his movie debut in the lead role of the comedy No Small Affair. The cast includes George Wendt, Jeffrey Tambor, Tim Robbins, E.G. Daily, Jennifer Tilly and, most notably, Demi Moore, who plays the romantic lead in the film. As revealed in his new memoir, So That Happened, Cryer and Moore briefly dated in real life too, which made for an interesting moment when Moore’s then-husband, Ashton Kutcher, joined the cast of Two and a Half Men.

Cryer also appeared in O.C. and Stiggs, which is probably one of the least-known films in the oeuvre of director Robert Altman. The film was barely even released, and the YouTube posting of it isn’t embeddable, so this will have to suffice: Cryer telling Seth Meyers about the time Altman pelted him with bird poop.

The comedy Morgan Stewart’s Coming Home stars Cryer as a horror-movie-loving weirdo whose eccentric personality becomes problematic when his dad runs for president. It was filmed before Pretty in Pink but released only after Pink became a smash hit. The film has its moments.

An admission: The author of this article watched Superman IV: The Quest for Peace many times as a child without realizing that Lenny Luthor, the punked-out nephew to Lex Luthor (Gene Hackman), was played by Jon Cryer. (The author also did not realize until much later that it’s considered one of the worst films ever made.)

Cryer got even more punked out for the 1987 feature Dudes. Directed by Penelope Spheeris, it’s just another one of those “bro-friends go on an adventure” movies, between The Boys Next Door and Wayne’s World.

Remember when joining the witness protection program was motivation enough for a fish-out-of-water comedy? In 1987’s Hiding Out, Cryer plays a murder target hiding out by posing as a high school student.

In 1989, CBS premiered The Famous Teddy Z, a sitcom about a mailroom clerk who becomes a Hollywood agent over night. The series costarred Jane Sibbett and Alex Rocco. Though Rocco’s character made a guest appearance on Murphy Brown, Teddy Z lasted only one season.

Everyone remembers that Charlie Sheen was in the 1991 spoof comedy Hot Shots! – but Cryer was too, meaning that when they starred in Two and a Half Men 12 years later, the actors were actually teaming up for the second time.

The success of Friends had other networks scrambling to imitate it, and one attempt, 1995’s very similar-sounding Partners, had Cryer starring alongside Maria Pitillo and Tate Donovan. Jennifer Aniston, who was dating Donovan at the time, guest-stars in the episode posted above.

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